Potassium Carbonate → (E)-N-(2-hydroxyphenethyl)-3-(3-pyridyl)-2-propenoic acid amide

HRID 428131

Reaktionsgleichung

[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](/[CH:7]=[CH:8]/[C:9]([OH:11])=O)[CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Br.[OH:19][C:20]1[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=1[CH2:22][CH2:23][NH2:24]>CN(C)C=O>[OH:19][C:20]1[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=1[CH2:22][CH2:23][NH:24][C:9](=[O:11])/[CH:8]=[CH:7]/[C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1

Komponenten

Reaktionsbedingungen

Temperatur: 40 °C

Versuchsvorschrift

Trans-3-(3-pyridyl)acrylic acid (22.35 g) and N,N′-carbonyldiimidazole (24.54 g) were dissolved in dimethylformamide (300 ml) and stirred at 40° C. for 40 minutes. Then, potassium carbonate (41.4 g) and 2-hydroxyphenethylamine hydrobromide (32.70 g) were added under room temperature and stirred for 1 hour. Insoluble materials were filtered out and the filtrate was concentrated under reduced pressure. Dilute hydrochloric acid was added to the residue under ice-cooling and stirring. The precipitated crystal was filtered out, washed with water, purified by silica gel column chromatography (chloroform:methanol=20:1) and then recrystallized in methanol to yield the titled compound (24.98 g, 62%).

Aufarbeitung

stirringstirred for 1 hour
filtrationInsoluble materials were filtered out
concentrationthe filtrate was concentrated under reduced pressure
additionDilute hydrochloric acid was added to the residue under ice-
temperaturecooling
stirringstirring
filtrationThe precipitated crystal was filtered out
washwashed with water
custompurified by silica gel column chromatography (chloroform:methanol=20:1)
customrecrystallized in methanol

Quellen und Nachweise

ORD-Eintrag: ord-6b0a221c5dbb4eeaa6dc2ab139ded584
Quelldatensatz: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06313153B1

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